Cycloalkanecarboxylic acids

The procedure described is essentially that of Shioiri and Yamada. Diphenyl phosphorazidate is a useful and versatile reagent in organic synthesis. It has been used for racemlzatlon-free peptide syntheses, thiol ester synthesis, a modified Curtius reaction, an esterification of a-substituted carboxylic acld, formation of diketoplperazines, alkyl azide synthesis, phosphorylation of alcohols and amines,and polymerization of amino acids and peptides. - Furthermore, diphenyl phosphorazidate acts as a nitrene source and as a 1,3-dipole.An example in the ring contraction of cyclic ketones to form cycloalkanecarboxylic acids is presented in the next procedure, this volume. 

Unsaturated acids are named using the name of the corresponding alkene, with the final -e replaced by -oic acid. The carbon chain is numbered starting with the carboxyl carbon, and a number gives the location of the double bond. The stereochemical terms cis and trails (and Z and E) are used as they are with other alkenes. Cycloalkanes with —COOH substituents are generally named as cycloalkanecarboxylic acids. 

With a dihaloalkane, rings can be formed by two sequential alkylation reactions this is an important way of making cycloalkanecarboxylic acids. Even the usually more difficult (see Chapter 42) four-membered rings can be made in this way. 

In agreement with these results Krapcho and Jahngen s attempts to utilize cyclopropanecarboxylic acid (216) in the reactions of a-anions of cycloalkanecarboxylic acid salts with cycloalkanones have been unsuccessful. 

Traynham and coworkers studied the anodic oxidation of medium-ring (7-10 carbon atoms) cycloalkanecarboxylic acids which yielded bicyclic products (22,23), among others, due to transannular elimination. 

Lactams are obtained from cycloalkanecarboxylic acids by treatment in chloroform solution at 65-70° with nitrosylsulfuric acid in 15-30% fuming sulfuric acid. ... 

Synthesis of cycloalkanecarboxylic acids from a,co-dihaloalkanes and diethyl sodiummalonate (see 1 st edition)... 

With other carboxylic acids, in particular cycloalkanecarboxylic acids, side reactions often occur. Thus barium cyclohexanecarboxylate gives, not cyclohexane, but a mixture of cyclohexene and cyclohexadiene.2... 

Cycloalkanecarboxylic acid A saturated cyclic carboxylic acid. 

In the lUPAC systematic nomenclature, the final e of the parent alkane is dropped, the suffix oic is added, and the separate word acid is added. Diacids are named similarly, except that the suffix is dioic, and the final e is not dropped. Cyclic acids are named as cycloalkanecarboxylic acids. Tahle 17.1 shows some common mono-and diacids along with some of their physical properties and common names, many of which are stfil used. 

To the extent possible, any carbon-carbon double or triple bonds that are present should be included in naming the main chain. Saturated cyclic acids are named as cycloalkanecarboxylic acids. Their aromatic counterparts are the benzoic acids. In these compounds, the carbon... 

In Summary The systematic naming of the carboxylic acids is based on the alkanoic acid stem. Cyclic derivatives are called cycloalkanecarboxylic acids, their aromatic counterparts are referred to as benzoic acids, and dicarboxylic systems are labeled alkanedioic acids. 

The malonic acid synthesis can be used to prepare cycloalkanecarboxylic acids by a double alkylation using a dihalide. Write the structure of the product of each of the steps in the following sequence. 

Straight- or branched-chain acids can be named either by their lUPAC names or by using Greek letters in conjunction with common names. Cycloalkanes with a —COOH substituent are named as cycloalkanecarboxylic acids-, that is, the ending "carboxylic acid" is combined with the name of the cycloalkane. Aromatic acids are named as derivatives of benzoic acid. Here are a few examples ... 

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